US9247735B2 - Crop plant-compatible herbicidal compositions containing herbicides and safeners - Google Patents
Crop plant-compatible herbicidal compositions containing herbicides and safeners Download PDFInfo
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- US9247735B2 US9247735B2 US13/009,031 US201113009031A US9247735B2 US 9247735 B2 US9247735 B2 US 9247735B2 US 201113009031 A US201113009031 A US 201113009031A US 9247735 B2 US9247735 B2 US 9247735B2
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- 239000000203 mixture Substances 0.000 title claims abstract description 76
- 239000004009 herbicide Substances 0.000 title claims abstract description 53
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 25
- 239000005586 Nicosulfuron Substances 0.000 claims abstract description 21
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 13
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 claims abstract description 12
- 239000005584 Metsulfuron-methyl Substances 0.000 claims abstract description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 11
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 5
- 150000002148 esters Chemical class 0.000 claims abstract description 5
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
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- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 claims description 15
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- 208000027418 Wounds and injury Diseases 0.000 claims description 11
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
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- 235000002678 Ipomoea batatas Nutrition 0.000 claims description 3
- 240000008415 Lactuca sativa Species 0.000 claims description 3
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- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 claims description 3
- 244000061176 Nicotiana tabacum Species 0.000 claims description 3
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- 235000007238 Secale cereale Nutrition 0.000 claims description 3
- 244000061456 Solanum tuberosum Species 0.000 claims description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 3
- 240000003829 Sorghum propinquum Species 0.000 claims description 3
- 235000011684 Sorghum saccharatum Nutrition 0.000 claims description 3
- 235000021536 Sugar beet Nutrition 0.000 claims description 3
- 235000020232 peanut Nutrition 0.000 claims description 3
- 240000000111 Saccharum officinarum Species 0.000 claims description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 claims description 2
- 235000019714 Triticale Nutrition 0.000 claims description 2
- 241000228158 x Triticosecale Species 0.000 claims description 2
- 244000299507 Gossypium hirsutum Species 0.000 claims 2
- 244000098338 Triticum aestivum Species 0.000 claims 1
- 239000005623 Thifensulfuron-methyl Substances 0.000 abstract description 31
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 abstract description 31
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- 150000003456 sulfonamides Chemical class 0.000 abstract description 13
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 abstract description 11
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- CTTHWASMBLQOFR-UHFFFAOYSA-N Amidosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)N(C)S(C)(=O)=O)=N1 CTTHWASMBLQOFR-UHFFFAOYSA-N 0.000 abstract description 3
- 239000005472 Bensulfuron methyl Substances 0.000 abstract description 3
- 239000005496 Chlorsulfuron Substances 0.000 abstract description 3
- WMLPCIHUFDKWJU-UHFFFAOYSA-N Cinosulfuron Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(OC)=N1 WMLPCIHUFDKWJU-UHFFFAOYSA-N 0.000 abstract description 3
- OFSLKOLYLQSJPB-UHFFFAOYSA-N Cyclosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)C2CC2)=N1 OFSLKOLYLQSJPB-UHFFFAOYSA-N 0.000 abstract description 3
- QNXAVFXEJCPCJO-UHFFFAOYSA-N Diclosulam Chemical compound N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1Cl QNXAVFXEJCPCJO-UHFFFAOYSA-N 0.000 abstract description 3
- UWVKRNOCDUPIDM-UHFFFAOYSA-N Ethoxysulfuron Chemical compound CCOC1=CC=CC=C1OS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 UWVKRNOCDUPIDM-UHFFFAOYSA-N 0.000 abstract description 3
- 239000005514 Flazasulfuron Substances 0.000 abstract description 3
- HWATZEJQIXKWQS-UHFFFAOYSA-N Flazasulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(F)(F)F)=N1 HWATZEJQIXKWQS-UHFFFAOYSA-N 0.000 abstract description 3
- 239000005529 Florasulam Substances 0.000 abstract description 3
- QZXATCCPQKOEIH-UHFFFAOYSA-N Florasulam Chemical compound N=1N2C(OC)=NC=C(F)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F QZXATCCPQKOEIH-UHFFFAOYSA-N 0.000 abstract description 3
- RXCPQSJAVKGONC-UHFFFAOYSA-N Flumetsulam Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(F)C=CC=C1F RXCPQSJAVKGONC-UHFFFAOYSA-N 0.000 abstract description 3
- 239000005534 Flupyrsulfuron-methyl Substances 0.000 abstract description 3
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- 239000005564 Halosulfuron methyl Substances 0.000 abstract description 3
- FMGZEUWROYGLAY-UHFFFAOYSA-N Halosulfuron-methyl Chemical group ClC1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC FMGZEUWROYGLAY-UHFFFAOYSA-N 0.000 abstract description 3
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- NAGRVUXEKKZNHT-UHFFFAOYSA-N Imazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N3C=CC=CC3=NC=2Cl)=N1 NAGRVUXEKKZNHT-UHFFFAOYSA-N 0.000 abstract description 3
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- VGHPMIFEKOFHHQ-UHFFFAOYSA-N Metosulam Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl VGHPMIFEKOFHHQ-UHFFFAOYSA-N 0.000 abstract description 3
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- 239000005592 Penoxsulam Substances 0.000 abstract description 3
- SYJGKVOENHZYMQ-UHFFFAOYSA-N Penoxsulam Chemical compound N1=C2C(OC)=CN=C(OC)N2N=C1NS(=O)(=O)C1=C(OCC(F)F)C=CC=C1C(F)(F)F SYJGKVOENHZYMQ-UHFFFAOYSA-N 0.000 abstract description 3
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- LTUNNEGNEKBSEH-UHFFFAOYSA-N Prosulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCC(F)(F)F)=N1 LTUNNEGNEKBSEH-UHFFFAOYSA-N 0.000 abstract description 3
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical group COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 abstract description 3
- NSWAMPCUPHPTTC-UHFFFAOYSA-N chlorimuron-ethyl Chemical group CCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 NSWAMPCUPHPTTC-UHFFFAOYSA-N 0.000 abstract description 3
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- BIKACRYIQSLICJ-UHFFFAOYSA-N cloransulam-methyl Chemical group N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1C(=O)OC BIKACRYIQSLICJ-UHFFFAOYSA-N 0.000 abstract description 3
- ZINJLDJMHCUBIP-UHFFFAOYSA-N ethametsulfuron-methyl Chemical group CCOC1=NC(NC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC)=N1 ZINJLDJMHCUBIP-UHFFFAOYSA-N 0.000 abstract description 3
- PXDNXJSDGQBLKS-UHFFFAOYSA-N foramsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(NC=O)C=2)C(=O)N(C)C)=N1 PXDNXJSDGQBLKS-UHFFFAOYSA-N 0.000 abstract description 3
- NIFKBBMCXCMCAO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoate Chemical group COC(=O)C1=CC=C(CNS(C)(=O)=O)C=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 NIFKBBMCXCMCAO-UHFFFAOYSA-N 0.000 abstract description 3
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- ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 abstract description 3
- VWGAYSCWLXQJBQ-UHFFFAOYSA-N methyl 4-iodo-2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=C(I)C=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 VWGAYSCWLXQJBQ-UHFFFAOYSA-N 0.000 abstract description 3
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003094 microcapsule Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- UWHURBUBIHUHSU-UHFFFAOYSA-N 2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoic acid Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 UWHURBUBIHUHSU-UHFFFAOYSA-N 0.000 description 1
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical class C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001057636 Dracaena deremensis Species 0.000 description 1
- 240000002024 Gossypium herbaceum Species 0.000 description 1
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 1
- 238000012695 Interfacial polymerization Methods 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- GOQNKRPYPIQLQG-UHFFFAOYSA-N OP(O)(O)=S.OP(O)(O)=S Chemical compound OP(O)(O)=S.OP(O)(O)=S GOQNKRPYPIQLQG-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- CHGJKHGLSDAYLS-UHFFFAOYSA-N [Mg].C(C)O.C(C)O Chemical compound [Mg].C(C)O.C(C)O CHGJKHGLSDAYLS-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000000460 chlorine Chemical group 0.000 description 1
- 229910052801 chlorine Chemical group 0.000 description 1
- 239000007931 coated granule Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 244000037671 genetically modified crops Species 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000003854 isothiazoles Chemical class 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 208000007578 phototoxic dermatitis Diseases 0.000 description 1
- 231100000018 phototoxicity Toxicity 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Definitions
- crop protection compositions which can be used against unwanted vegetation and which contain, as active compounds, a combination of at least one herbicide and at least one safener.
- Herbicides are useful for controlling unwanted vegetation, i.e. weeds, which may otherwise cause significant damage to desirable plant species such as crop plants or ornamentals.
- Many potent herbicides have the ability to control for full growing seasons and at low rates of application, a broad spectrum of grass and broadleaf weeds that compete with desirable plants or crops such as wheat, cotton, or corn.
- certain potent herbicides are not tolerated by, or are phytotoxic to, a wide of desirable plants when applied at rates effective to control unwanted vegetation.
- a large number of sulfonamide or sulfonylurea herbicides cannot thus be employed in maize, rice or cereals with sufficient selectivity.
- Phytotoxic side-effects become apparent on the crop plants in particular when these herbicides are applied post-emergence, and it is desirable to avoid or reduce such a phytotoxicity.
- 5-phenylisoxazoline- and 5-phenylisothiazoline-3-carboxyl derivatives as safeners for herbicides from the series of the carbamates, thiocarbamates, haloacetanilides, phenoxyphenoxyalkanecarboxylic acid derivatives, sulfonylureas and the like has been mentioned in EP-A-509433.
- EP-A-520371 mentions, inter alia, 5-alkylisoxazoline- and -isothiazoline-3-carboxyl derivatives as safeners for a range of classes of herbicides.
- WO92/03053 mentions the use of substituted 3-arylisoxazoine- and -isothiazoline-5-carboxyl derivatives as safeners for certain herbicides.
- WO 91/18907 describes silyl-substituted isoxazolines, isoxazoles, isothiazolines and isothiazoles as crop protecting agents.
- the use of the herbicidal compositions mentioned in these publications is frequently associated with one or more disadvantages.
- the herbicidal activity of the known compounds is not always sufficient, or, if the herbicidal activity is sufficient, then undesired damage to the useful plants can be observed.
- U.S. Pat. No. 6,855,667 mentions the use of certain aromatic phosphate esters and thioesters as safeners for the herbicide clomazone. While other herbicides are mentioned in the disclosure, the only herbicide specifically exemplified is clomazone, and the only test results were on corn and cotton seeds; no results are provided for post-emergence application. Moreover, the only test results provided were for a single safener, dietholate, and the largest percent reduction in injury obtained was only 80.0%. This latter value was obtained by applying the safening compound to seeds as a seed treatment, and then later applying clomazone. The average reduction in injury reported in the patent was only 33.35% for cotton seed treatment and only 36.8% for both types of corn seed tested.
- herbicidal compositions characterized in that they comprise:
- the herbicides rimsulfuron, thifensulfuron-methyl, nicosulfuron, tribenuron-methyl, metsulfuron-methyl, and combinations thereof are particularly suitable for use as component B.
- compositions comprise component A and B in a weight ratio of A to B ranging from 1:10 to 10:1, in particular from 1:10 to 5:1.
- T and T 1 are individually alkyl having 1-10 carbon atoms, more particularly, alkyl having 1-7 carbon atoms, even more particularly, alkyl having 1-4 carbon atoms are suitable for use as component A.
- Particularly suitable are compounds wherein T and T 1 are individually methyl, ethyl, propyl, or butyl, U is sulfur, and V, W, X, Y, and Z are each hydrogen.
- Also disclosed herein is a method of protecting a plant from unintentional phytotoxic injury from application of a herbicidally-effective amount of a herbicidal compound to the locus of the plant, which method comprises applying to said locus an effective amount of one or more safening compounds phosphorated esters of the formula (I).
- the method comprises applying to the locus of the plant the composition described above, wherein the herbicide and safener are applied simultaneously.
- the embodiments disclosed herein generally relate to the field of crop protection compositions which can be used against unwanted vegetation and which comprise, as active compounds, a combination of at least one herbicide and at least one safener selected from phosphorated esters of the formula (I):
- alkyl, alkenyl, alkynyl, alkoxy, and haloalkyl used alone or as part of a larger moiety, includes straight or branched chains of at least one or two carbon atoms, as appropriate to the substituent, and preferably up to 12 carbon atoms, more preferably up to ten carbon atoms, most preferably up to seven carbon atoms.
- Halogen or “halo” refers to fluorine, bromine, iodine, or chlorine.
- the herbicidal compound or compounds include sulfonylureas and/or sulfonamides selected from the group consisting of amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flupyrsulfuron-methyl, flazasulfuron, foramsulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron-methyl, mesosulfuron-methyl, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-
- rimsulfuron and thifensulfuron-methyl, thifensulfuron-methyl and tribenuron-methyl, rimsulfuron and nicosulfuron, and thifensulfuron-methyl and metsulfuron-methyl are particularly suitable.
- Plants of interest that can be safened as described herein preferably include, without limitation, soybean, cotton, sugarbeet, rape, potato, sunflower, peanut, lettuce, carrot, sweet potato, alfalfa, tobacco, corn, rice, sorghum, wheat, barley, oats, rye, triticale, and sugarcane. More preferred plants on which to apply the compounds or the compositions of the present invention are soybean, wheat, corn, cotton, sugarbeet, rape, potato, sunflower, peanut, lettuce, carrot, sweet potato, alfalfa, and tobacco. The most preferred plants to which methods and compositions described herein are applied are wheat, corn, and cotton, especially corn and cotton.
- the herbicidal active substances and the safener mentioned can be applied together (in the form of a ready-mix or by the tank mix method) or one after the other in any desired sequence.
- the ratio by weight of safener to herbicide can vary within wide limits and is preferably in a range of 1:10 to 10:1, in particular in a range of 1:10 to 5:1.
- the precise amounts of herbicide and safener which are used in each case will depend on the type of the herbicide used and/or on the safener used, as well on the nature of the plant to be treated, and can be determined in each individual case by using the information provided herein, as well as routine experimentation and suitable preliminary trials. Analogous ratios can be considered when safener and other active substances of crops protection products, such as insecticides or insecticide/herbicide combinations, are used.
- the safeners are desirably mainly employed in cereal crops (wheat, rye, barley, oats), rice, maize, sorghum, but also in cotton and corn.
- a particular advantage of the safener of the formula (I) described herein is to be found when they are combined with herbicides selected from the group consisting of the sulfonylureas and/or sulfonamides.
- Some herbicides of these structural classes cannot be employed, e.g., in cotton and corn, or cannot be employed with sufficient selectivity, without the safeners and techniques described herein.
- Outstanding and surprising selectivities can be achieved even with these difficult-to-employ herbicides in cotton and corn when the herbicides are combined with a safener according to the compositions and/or methods described herein.
- the safener of the formula (I) can be used for pre-treating the seed of the crop plant, or they can be incorporated into the seed furrows prior to sowing, or applied together with the herbicidal before or after emergence of the plants.
- Pre-emergence treatment includes both the treatment of the area under cultivation before sowing and treatment of the area under cultivation where seed has been sown, but growth of the crop plants has not yet taken place.
- the joint use together with the herbicide, in particular by post-emergence methods, is preferred.
- Tank mixes or ready-mixes can be employed for this purpose. Any of these application methods are within the meaning of the term “applying to the locus of the plant,” as that term is used herein.
- the application rates of safener required can vary within wide limits and are, as a rule, in the range of 0.001 to 15 kg, preferably 0.005 to 5 kg, of active substance per hectare.
- the compositions may contain additional pesticidal materials, including additional herbicides, such as fluoroxypyr.
- additional herbicides such as fluoroxypyr.
- the combination of thifensulfuron-methyl and fluoroxypyr is particularly suitable.
- crop-protecting products which comprise an active substance of the formula (I) and customary formulation auxiliaries, as well as to pesticidal, preferably herbicidal, compositions which comprise an active substance of the formula (I), and a pesticide or herbicide and formulation auxiliaries which are customarilly used in the field of crop protection.
- the compounds of the formula (I) and/or their combinations with one or more of the herbicides mentioned can be formulated in a variety of ways, as determined by various biological and/or chemical-physical parameters.
- the following possibilities are therefore among those suitable for formulation: wettable powders (WP), emulsifiable concentrates (EC), water soluble powders (SP), water-soluble concentrates (SL), concentrated emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions or emulsions, capsules suspensions (CS), oil- or water-based dispersions (SC), suspoemulsions, dusts (DP), seed-dressing products, granules (GR) in the form of microgranules, spray granules, coated granules and adsorption granules, water-soluble granules (SG), water-dispersible granules (WG), ULV formulations, microcapsules and waxes.
- Wettable powders are preparations which are uniformly dispersible in water and which, besides the active substance, also contain wetting agents, for example polyoxethylated alkylphenols, polyoxethylated fatty alcohols and fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates or alkylarylsulfonates, and dispersing agents, for example sodium lignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate, in addition to a diluent or inert substance.
- wetting agents for example polyoxethylated alkylphenols, polyoxethylated fatty alcohols and fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates or al
- Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons, with addition of one or more emulsifiers.
- organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons.
- emulsifiers which can be used include: calcium alkylarylsulfonates, such as calcium dodecylbenzenesulfonate, or non-ionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide ethylene oxide condensation products (for example block copolymers), alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.
- calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate
- non-ionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide ethylene oxide condensation products (for example block copolymers), alkyl polyethers, sorbitan fatty acid est
- Dusts are obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
- finely divided solid substances for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
- Granules can be prepared either by spraying a liquid containing the active substance onto adsorptive, granulated inert material or by applying active substance concentrates onto the surface of carriers, such as sand, kaolin or granulated inert material, by means of binders, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active substances can also be granulated in the manner which is conventional for the production of fertilizer granules, if desired in the form of a mixture with fertilizers.
- the agrochemical preparations typically contain approximately 0.1 to 99 percent by weight, in particular approximately 0.1 to 95% by weight, of active substances of the formula (I) (antidote) or of the active substance mixture of antidote/herbicide, and approximately 1 to 99.9% by weight, in particular approximately 5 to 99.8% by weight, of a solid or liquid additive, and approximately 0 to 25% by weight, in particular approximately 0.1 to 25% by weight, of a surfactant.
- the concentration of active substance in wettable powders is, for example, approximately 10 to 90% by weight, the remainder to 100% being composed of customary formulation components. In the case of emulsifiable concentrates, the concentration of active substance is approximately 1 to 80% by weight of active substances. Formulations in the form of dusts contain approximately 1 to 20% by weight of active substances, sprayable solutions approximately 0.2 to 20% by weight of active substances. In the case of granules, such as water-dispersible granules, the active substance content depends partly on whether the active compound is in liquid or solid form. In general, the water-dispersible granules typically contain between 10 and 90% by weight of active substance.
- the active substances, the formulations mentioned contain, if appropriate, the adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers which are conventional in each case.
- the formulations when provided in commercially available form, are, if appropriate, diluted in the customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Preparations in the form of dusts, granules and sprayable solutions are conventionally not diluted any further with other inert substances before they are used.
- the application rate of the antidotes required varies with the external conditions such as inter alia, temperature, humidity, and the nature of the pesticide or herbicide used.
- the term “technical” means the herbicidal compound as it is obtained from the manufacturing process, and typically includes 90-100 wt % of the active ingredient, with the remainder being inert additives, impurities, etc. All percentages are by weight, based upon the total weight of the composition.
- EXAMPLE 1 22.4% COMPARISON A: 22.4% Rimsulfuron + Thifensulfuron Rimsulfuron + Thifensulfuron methyl WG (with safener) methyl WG (without safener) Component Composition Component Composition Remark Rimsulfuron (technical) 18.4% Rimsulfuron (technical) 18.4% Active ingredient Thifensulfuron (techical) 4% Thifensulfuron (technical) 4% Active ingredient O,O-dimethyl-O-phenyl 2.3% O,O-dimethyl-O-phenyl 0 safener phosphorothioate phosphorothioate Sodium 12% Sodium 12% Dispersing dodecylphenylsulfonate dodecylphenylsulfonate agent Naphthalene sulphonate, 3% Naphthalene sulphonate, 3% Wetting sodium salt sodium salt agent Mannitol Balance to Mannitol
- the water-dispersible granules are obtained by mixing the above components according to the recipe, and grinding the mixture in a pine-disc mill to form a powder, and then granulating the powder in a fluidized bed by spraying on water as granulation liquid.
- EXAMPLE 2 54.5% COMPARISON B: 54.5% Nicosulfuron WG (with safener) Nicosulfuron WG (without safener) Component Composition Component Composition Remark Nicosulfuron (technical) 54.5% Nicosulfuron (technical) 54.5% Active ingredient O,O-dimethyl-O-phenyl 13.6% O,O-dimethyl-O-phenyl 0 safener phosphorothioate phosphorothioate Sodium 10% Sodium 10% Dispersing dodecylphenylsulfonate dodecylphenylsulfonate agent Naphthalene sulphonate, 2.6% Naphthalene sulphonate, 2.6% Wetting sodium salt sodium salt agent Mannitol Balance to Mannitol Balance to filler 100% 100%
- the water-dispersible granules are obtained by mixing the above components according to the recipe, and grinding the mixture in a pine-disc mill to form a powder, and then granulating the powder in a fluidized bed by spraying on water as granulation liquid.
- the water-dispersible granules are obtained by mixing the above components according to the recipe, and grinding the mixture in a pine-disc mill to form a powder, and then granulating the powder in a fluidized bed by spraying on water as granulation liquid.
- EXAMPLE 4 40 g/L Nicosulfuron OD COMPARISON D: 40 g/L (with safener) Nicosulfuron OD (without safener) Component Composition Component Composition Remark Nicosulfuron (technical) 50% Nicosulfuron (technical) 50% Active ingredient O,O-diethyl-O-phenyl 10% O,O-diethyl-O-phenyl 0 safener phosphorothioate phosphorothioate Sodium 5% Sodium 5% Dispersing dodecylphenylsulfonate dodecylphenylsulfonate agent Nonyl phenoxy 5% Nonyl phenoxy 5% Co-dispersing polyethyleneoxy polyethyleneoxy agent ethanol ethanol Magnesium Aluminium 0.5% Magnesium Aluminium 0.5% Thickening Silicate Silicate agent Vegetable oil Balance to Vegetable oil Balance to diluent 100% 100% The oil-base suspension concentrate are obtained by mixing all the above components according to the recipe
- the soluble granules are obtained by mixing the above components according to the recipe, and grinding the mixture in a pine-disc mill to form a powder, and then granulating the powder in a fluidized bed by spraying on water as granulation liquid.
- EXAMPLE 6 COMPARISON F: Thifensulfuron methyl 18 g/L + Thifensulfuron methyl 18 g/L + Fluroxypyr 180 g/L ZC (with safener) Fluroxypyr 180 g/L ZC(without safener) Component Composition Component Composition Remark Thifensulfuron (technical) 18 g Thifensulfuron (technical) 18 g Active ingredient Fluroxypyr (technical) 180 g Fluroxypyr (technical) 180 g Active ingredient O,O-dipropyl-O-phenyl 90 g O,O-dipropyl-O-phenyl 0 safener phosphorothioate phosphorothioate Atlox 4913 40 g Atlox 4913 40 g Atlox 4913 40 g Dispersing agent Citric acid 0.5 g Citric acid 0.5 g acid Triethyl amine 20% emulsion 1 g Triethyl amine 20%
- Fluoroxypyr CS preparation The PAPI and Fluoroxypyr were combined with stirring to form a uniform liquid mixture. A solution of Atlox 4913 in water was heated in a Waring blender cup to about 50° C. The solution was agitated while the liquid mixture was slowly added, to form a uniform emulsion of the water immiscible phase dispersed evenly throughout the continuous aqueous phase. The aqueous solution of triethyl amine was added slowly, upon which interfacial polymerization occurred, producing microcapsules having a particle size of from 1 to 30 microns. The resulting product was cooled and filtered, to obtain a stable CS formulation of microencapsulated fluoroxypyr.
- Thifensulfuron SC preparation Atlox 4913, thifensulfuron-methyl, safener and water were combined with mixing and finely milled to form a suspension concentrate (SC).
- EXAMPLE 7 75% COMPARISON G: 75% Thifensulfuron-methyl WG Thifensulfuron-methyl WG (with safener) (without safener) Component Composition Component Composition Remark Thifensulfuron-methyl 75% Thifensulfuron-methyl 75% Active (technical) (techical) ingredient O,O-dibutyl-O-phenyl 10% O,O-dibutyl-O-phenyl 0 safener phosphorothioate phosphorothioate Sodium 5% Sodium 5% Dispersing dodecylphenylsulfonate dodecylphenylsulfonate agent Naphthalene sulphonate, 2.6% Naphthalene sulphonate, 2.6% Wetting sodium salt sodium salt agent Mannitol Balance to Mannitol Balance to filler 100% 100%
- the water-dispersible granules are obtained by mixing the above components according to the recipe, and grinding the mixture in a pine-disc mill to form a powder, and then granulating the powder in a fluidized bed by spraying on water as granulation liquid.
- EXAMPLE 8 68.2% COMPARISON H: 68.2% Thifensulfuron-methyl + 6.8% Metsulfuron Thifensulfuron-methyl + 6.8% Metsulfuron methyl WG (with safener) methyl WG (without safener) Component Composition Component Composition Remark Thifensulfuron-methyl 68.2% Thifensulfuron-methyl 68.2% Active (technical) (technical) ingredient Metsulfuron-methyl 6.8% Metsulfuron-methyl 6.8% Active (technical) (technical) ingredient O,O-dibutyl-O-phenyl 15% O,O-dibutyl-O-phenyl 0 safener phosphorothioate phosphorothioate Sodium 3% Sodium 3% Dispersing dodecylphenylsulfonate dodecylphenylsulfonate agent Naphthalene sulphonate, 1.6% Naphthalene sul
- the water-dispersible granules are obtained by mixing the above components according to the recipe, and grinding the mixture in a pine-disc mill to form a powder, and then granulating the powder in a fluidized bed by spraying on water as granulation liquid.
- compositions are therefore suitable for a side-by-side comparison illustrating the unexpected advantages of the combination of a sulfonylurea and/or sulfonamide herbicide and a safener as described herein.
- Example 1 to Example 8 and of Comparison A to Comparison H are applied in the form of aqueous suspensions at an application rate of 300 L of water/ha (converted). 4 weeks after the treatment, the plants are scored for phytotoxicity of the applied composition, and the extent of the damage is determined by comparison with the results of treatment with Comparison A to Comparison H.
- test results show in table 1, 2, 3 and 4 demonstrate that the compounds with safeners as described herein can prevent damage to plants in highly efficient manner.
- Example 7/Comparison G (4-leaf stage) is even close to the reductions obtained for dietholate with clomazone as reported in U.S. Pat. No. 6,855,667; all of the remaining reductions in injury are surprisingly well above the results obtained for clomazone.
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Abstract
-
- A) an antidotically effective amount of one or more safeners from the group of the phosphorated esters of the formula (I):
-
- T and T1 are independently selected from the group of hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkenyl, and alkynyl;
- U is O or S, and
- V, W, X, Y, and Z are independently selected from the group of hydrogen, halogen, alkyl, haloalkyl, and alkoxy; and
- B) one or more sulfonamide or sulfonylurea herbicides selected from the group consisting of amidosulfuron, azimsulfuro bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flupyrsulfuron-methyl, flazasulfuron, foramsulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron-methyl, mesosulfuron-methyl, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, prosulfuron, thifensulfuron-methyl, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl, triosulfuron, cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, and combinations thereof, and methods for using the same.
Description
-
- A) an antidotically effective amount of one or more safeners from the group of the phosphorated esters of the formula (I):
- T and T1 are independently selected from the group of hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkenyl, and alkynyl;
- U is O or S, and
- V, W, X, Y, and Z are independently selected from the group of hydrogen, halogen, alkyl, haloalkyl, and alkoxy; and
- B) one or more sulfonamide or sulfonylurea herbicides selected from the group consisting of amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flupyrsulfuron-methyl, flazasulfuron, foramsulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron-methyl, mesosulfuron-methyl, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, prosulfuron, thifensulfuron-methyl, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl, triosulfuron, cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, and combinations thereof.
- T and T1 are independently selected from the group of hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkenyl, and alkylnyl;
- U is O or S, and
- V, W, X, Y, and Z are independently selected from the group of hydrogen, halogen, alkyl, haloalkyl, and alkoxy.
EXAMPLE 1: 22.4% | COMPARISON A: 22.4% | |
Rimsulfuron + Thifensulfuron | Rimsulfuron + Thifensulfuron | |
methyl WG (with safener) | methyl WG (without safener) |
Component | Composition | Component | Composition | Remark |
Rimsulfuron (technical) | 18.4% | Rimsulfuron (technical) | 18.4% | Active |
ingredient | ||||
Thifensulfuron (techical) | 4% | Thifensulfuron (technical) | 4% | Active |
ingredient | ||||
O,O-dimethyl-O-phenyl | 2.3% | O,O-dimethyl-O-phenyl | 0 | safener |
phosphorothioate | phosphorothioate | |||
Sodium | 12% | Sodium | 12% | Dispersing |
dodecylphenylsulfonate | dodecylphenylsulfonate | agent | ||
Naphthalene sulphonate, | 3% | Naphthalene sulphonate, | 3% | Wetting |
sodium salt | sodium salt | agent | ||
Mannitol | Balance to | Mannitol | Balance to | filler |
100% | 100% | |||
EXAMPLE 2: 54.5% | COMPARISON B: 54.5% | |
Nicosulfuron WG (with safener) | Nicosulfuron WG (without safener) |
Component | Composition | Component | Composition | Remark |
Nicosulfuron (technical) | 54.5% | Nicosulfuron (technical) | 54.5% | Active |
ingredient | ||||
O,O-dimethyl-O-phenyl | 13.6% | O,O-dimethyl-O-phenyl | 0 | safener |
phosphorothioate | phosphorothioate | |||
Sodium | 10% | Sodium | 10% | Dispersing |
dodecylphenylsulfonate | dodecylphenylsulfonate | agent | ||
Naphthalene sulphonate, | 2.6% | Naphthalene sulphonate, | 2.6% | Wetting |
sodium salt | sodium salt | agent | ||
Mannitol | Balance to | Mannitol | Balance to | filler |
100% | 100% | |||
EXAMPLE 3: 75% | COMPARISON C: 75% | |
Thifensulfuron-methyl + | Thifensulfuron-methyl + | |
Tribenuron-methyl WG (with safener) | Tribenuron-methyl WG (without safener) |
Component | Composition | Component | Composition | Remark |
Thifensulfuron-methyl | 50% | Thifensulfuron-methyl | 50% | Active |
(technical) | (technical) | ingredient | ||
Tribenuron-methyl | 25% | Tribenuron-methyl | 25% | Active |
(technical) | (technical) | ingredient | ||
O,O-dimethyl-O-phenyl | 10% | O,O-dimethyl-O-phenyl | 0 | safener |
phosphorothioate | phosphorothioate | |||
Sodium | 5% | Sodium | 5% | Dispersing |
dodecylphenylsulfonate | dodecylphenylsulfonate | agent | ||
Naphthalene sulphonate, | 2.6% | Naphthalene sulphonate, | 2.6% | Wetting |
sodium salt | sodium salt | agent | ||
Mannitol | Balance to | Mannitol | Balance to | filler |
100% | 100% | |||
EXAMPLE 4: 40 g/L Nicosulfuron OD | COMPARISON D: 40 g/L | |
(with safener) | Nicosulfuron OD (without safener) |
Component | Composition | Component | Composition | Remark |
Nicosulfuron (technical) | 50% | Nicosulfuron (technical) | 50% | Active |
ingredient | ||||
O,O-diethyl-O-phenyl | 10% | O,O-diethyl-O-phenyl | 0 | safener |
phosphorothioate | phosphorothioate | |||
Sodium | 5% | Sodium | 5% | Dispersing |
dodecylphenylsulfonate | dodecylphenylsulfonate | agent | ||
Nonyl phenoxy | 5% | Nonyl phenoxy | 5% | Co-dispersing |
polyethyleneoxy | polyethyleneoxy | agent | ||
ethanol | ethanol | |||
Magnesium Aluminium | 0.5% | Magnesium Aluminium | 0.5% | Thickening |
Silicate | Silicate | agent | ||
Vegetable oil | Balance to | Vegetable oil | Balance to | diluent |
100% | 100% | |||
The oil-base suspension concentrate are obtained by mixing all the above components according to the recipe, and milling the mixture using a horizontal agitating bead mill maintaining appropriate process parameters, such as the average particle size, as is conventional in this field.
EXAMPLE 5: 22.4% | COMPARISON E: 22.4% | |
Rimsulfuron + Nicosulfuron | Rimsulfuron + Nicosulfuron | |
SG (with safener) | SG(without safener) |
Component | Composition | Component | Composition | Remark |
Rimsulfuron (technical) | 10% | Rimsulfuron (technical) | 10% | Active |
ingredient | ||||
Nicosulfuron (technical) | 10% | Nicosulfuron (technical) | 10% | Active |
ingredient | ||||
O,O-diethyl-O-phenyl | 20% | O,O-diethyl-O-phenyl | 0 | safener |
phosphorothioate | phosphorothioate | |||
Sodium | 12% | Sodium | 12% | Dispersing |
dodecylphenylsulfonate | dodecylphenylsulfonate | agent | ||
Naphthalene sulphonate, | 3% | Naphthalene sulphonate, | 3% | Wetting |
sodium salt | sodium salt | agent | ||
Mannitol | Balance to | Mannitol | Balance to | filler |
100% | 100% | |||
EXAMPLE 6: | COMPARISON F: | |
Thifensulfuron methyl 18 g/L + | Thifensulfuron methyl 18 g/L + | |
Fluroxypyr 180 g/L ZC (with safener) | Fluroxypyr 180 g/L ZC(without safener) |
Component | Composition | Component | Composition | Remark |
Thifensulfuron (technical) | 18 | g | Thifensulfuron (technical) | 18 | g | Active |
ingredient | ||||||
Fluroxypyr (technical) | 180 | g | Fluroxypyr (technical) | 180 | g | Active |
ingredient |
O,O-dipropyl-O-phenyl | 90 | g | O,O-dipropyl-O-phenyl | 0 | safener |
phosphorothioate | phosphorothioate |
Atlox 4913 | 40 | g | Atlox 4913 | 40 | g | Dispersing |
agent | ||||||
Citric acid | 0.5 | g | Citric acid | 0.5 | g | acid |
Triethyl amine 20% emulsion | 1 | g | Triethyl amine 20% emulsion | 1 | g | catalysit |
PAPI | 13.5 | g | PAPI | 13.5 | g | Wall-forming |
agent |
water | Balance to | water | Balance to | diluent |
1 L | 1 L | |||
EXAMPLE 7: 75% | COMPARISON G: 75% | |
Thifensulfuron-methyl WG | Thifensulfuron-methyl WG | |
(with safener) | (without safener) |
Component | Composition | Component | Composition | Remark |
Thifensulfuron-methyl | 75% | Thifensulfuron-methyl | 75% | Active |
(technical) | (techical) | ingredient | ||
O,O-dibutyl-O-phenyl | 10% | O,O-dibutyl-O-phenyl | 0 | safener |
phosphorothioate | phosphorothioate | |||
Sodium | 5% | Sodium | 5% | Dispersing |
dodecylphenylsulfonate | dodecylphenylsulfonate | agent | ||
Naphthalene sulphonate, | 2.6% | Naphthalene sulphonate, | 2.6% | Wetting |
sodium salt | sodium salt | agent | ||
Mannitol | Balance to | Mannitol | Balance to | filler |
100% | 100% | |||
EXAMPLE 8: 68.2% | COMPARISON H: 68.2% | |
Thifensulfuron-methyl + 6.8% Metsulfuron | Thifensulfuron-methyl + 6.8% Metsulfuron | |
methyl WG (with safener) | methyl WG (without safener) |
Component | Composition | Component | Composition | Remark |
Thifensulfuron-methyl | 68.2% | Thifensulfuron-methyl | 68.2% | Active |
(technical) | (technical) | ingredient | ||
Metsulfuron-methyl | 6.8% | Metsulfuron-methyl | 6.8% | Active |
(technical) | (technical) | ingredient | ||
O,O-dibutyl-O-phenyl | 15% | O,O-dibutyl-O-phenyl | 0 | safener |
phosphorothioate | phosphorothioate | |||
Sodium | 3% | Sodium | 3% | Dispersing |
dodecylphenylsulfonate | dodecylphenylsulfonate | agent | ||
Naphthalene sulphonate, | 1.6% | Naphthalene sulphonate, | 1.6% | Wetting |
sodium salt | sodium salt | agent | ||
Mannitol | Balance to | Mannitol | Balance to | filler |
100% | 100% | |||
TABLE 1 |
Effect of the compositions described herein on cotton plants |
Dosage rate | Herbicidal activity in cotton(in %) |
Examples | (kg a.i./ha) | 4-leaf stage | 6-leaf stage |
Example 1 | 0.2 | 5 | 0 |
Comparison A | 0.2 | 75 | 60 |
Exmaple2 | 0.2 | 0 | 0 |
Comparison B | 0.2 | 80 | 77 |
Example 3 | 0.2 | 0 | 0 |
Comparison C | 0.2 | 78 | 86 |
Example 4 | 0.2 | 0 | 0 |
Comparison D | 0.2 | 40 | 30 |
Example 5 | 0.2 | 0 | 0 |
Comparison E | 0.2 | 40 | 30 |
Example 6 | 0.2 | 0 | 0 |
Comparison F | 0.2 | 30 | 25 |
Example 7 | 0.2 | 10 | 5 |
Comparison G | 0.2 | 83 | 80 |
Example 8 | 0.2 | 5 | 0 |
Comparison H | 0.2 | 85 | 82 |
TABLE 2 |
Effect of the compositions described herein on corn plants |
Dosage rate | Herbicidal activity in corn (in %) |
Examples | (kg a.i./ha) | 4-leaf stage | 6-leaf stage |
Example 1 | 0.3 | 5 | 0 |
Comparison A | 0.3 | 80 | 75 |
Example 2 | 0.3 | 0 | 0 |
Comparison B | 0.3 | 85 | 88 |
Example 3 | 0.3 | 10 | 5 |
Comparison C | 0.3 | 90 | 85 |
Example 4 | 0.3 | 0 | 0 |
Comparison D | 0.3 | 40 | 30 |
Example 5 | 0.3 | 0 | 0 |
Comparison E | 0.3 | 10 | 15 |
Example 6 | 0.3 | 0 | 0 |
Comparison F | 0.3 | 15 | 13 |
Example 7 | 0.3 | 15 | 5 |
Comparison G | 0.3 | 90 | 88 |
Example 8 | 0.3 | 10 | 5 |
Comparison H | 0.3 | 92 | 88 |
TABLE 3 |
Effect of the compositions described herein on rice plants |
Dosage rate | Herbicidal activity in rice (in %) |
Examples | (kg a.i./ha) | 4-leaf stage | 6-leaf stage |
Example 1 | 0.075 | 5 | 0 |
Comparison A | 0.075 | 70 | 65 |
Example 2 | 0.075 | 0 | 0 |
Comparison B | 0.075 | 75 | 78 |
Example 3 | 0.075 | 10 | 5 |
Comparison C | 0.075 | 70 | 75 |
Example 4 | 0.075 | 0 | 0 |
Comparison D | 0.075 | 40 | 20 |
Example 5 | 0.075 | 0 | 0 |
Comparison E | 0.075 | 10 | 15 |
Example 6 | 0.075 | 0 | 0 |
Comparison F | 0.075 | 15 | 13 |
Example 7 | 0.075 | 10 | 0 |
Comparison G | 0.075 | 80 | 78 |
Example 8 | 0.075 | 5 | 0 |
Comparison H | 0.075 | 82 | 78 |
TABLE 4 |
Effect of the compositions described herein on barley plants |
Dosage rate | Herbicidal activity in barley (in %) |
Examples | (kg a.i./ha) | 4-leaf stage | 6-leaf stage |
Example 1 | 0.2 | 5 | 0 |
Comparison A | 0.2 | 69 | 67 |
Example 2 | 0.2 | 0 | 0 |
Comparison B | 0.2 | 73 | 75 |
Example 3 | 0.2 | 7 | 4 |
Comparison C | 0.2 | 74 | 70 |
Example 4 | 0.2 | 0 | 0 |
Comparison D | 0.2 | 36 | 23 |
Example 5 | 0.2 | 0 | 0 |
Comparison E | 0.2 | 12 | 13 |
Example 6 | 0.2 | 0 | 0 |
Comparison F | 0.2 | 17 | 13 |
Example 7 | 0.2 | 10 | 0 |
Comparison G | 0.2 | 80 | 74 |
Example 8 | 0.2 | 5 | 0 |
Comparison H | 0.2 | 85 | 74 |
Claims (24)
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/009,031 US9247735B2 (en) | 2011-01-19 | 2011-01-19 | Crop plant-compatible herbicidal compositions containing herbicides and safeners |
PCT/CN2011/081898 WO2012097629A1 (en) | 2011-01-19 | 2011-11-08 | Crop plant-compatible herbicidal compositions containing herbicides and safeners |
BR112013018077-3A BR112013018077B1 (en) | 2011-01-19 | 2011-11-08 | HERBICIDE COMPOSITIONS COMPATIBLE WITH THE PLANT CROP CONTAINING HERBICIDES AND PROTECTIVE AGENTS |
CA2834948A CA2834948C (en) | 2011-01-19 | 2011-11-08 | Crop plant-compatible herbicidal compositions containing herbicides and safeners |
EP11856014.3A EP2665359B1 (en) | 2011-01-19 | 2011-11-08 | Crop plant-compatible method of using herbicides and safeners |
CN201110442376.4A CN102599152B (en) | 2011-01-19 | 2011-12-26 | Comprise the Herbicidal combinations compatible with crop plants of herbicide and safener |
CZ2011-898A CZ308313B6 (en) | 2011-01-19 | 2011-12-29 | A herbicidal composition comprising a safener and a herbicide and a method of protecting plants from phytotoxic damage by a herbicide |
TW101101386A TWI527517B (en) | 2011-01-19 | 2012-01-13 | Herbicidal composition and applying method thereof |
FR1250394A FR2970399B1 (en) | 2011-01-19 | 2012-01-16 | HERBICIDE COMPOSITIONS COMPATIBLE WITH CULTIVATED PLANTS CONTAINING HERBICIDES AND PHYTOPROTECTIVE |
ARP120100149A AR085078A1 (en) | 2011-01-19 | 2012-01-16 | HERBICIDE COMPOSITIONS COMPATIBLE WITH CROP PLANTS CONTAINING HERBICIDES AND PHYTOPROTECTORS |
MA34548A MA34427B1 (en) | 2011-01-19 | 2012-01-17 | HERBICIDE COMPOSITIONS COMPATIBLE WITH CULTIVATED PLANTS CONTAINING HERBICIDES AND PHYTOPROTECTORS. |
UAA201200538A UA104032C2 (en) | 2011-01-19 | 2012-01-18 | Herbicidal compositions, compatible with cultivated plants, comprising herbicides and safeners |
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WO2012135441A1 (en) * | 2011-03-30 | 2012-10-04 | Dow Agrosciences Llc | Penoxsulam as an herbicide in alfalfa |
US9888683B2 (en) * | 2011-12-29 | 2018-02-13 | Akzo Nobel Chemicals International B.V. | Macrostructure forming surfactants useful as spray drift control agents in pesticide spraying applications |
AR100785A1 (en) * | 2014-06-09 | 2016-11-02 | Dow Agrosciences Llc | HERBICIDE CONTROL OF MALEZA FROM COMBINATIONS OF FLUROXIPIR AND INHIBITORS OF ALS |
TWI689252B (en) | 2014-09-15 | 2020-04-01 | 美商陶氏農業科學公司 | Synergistic weed control from applications of pyridine carboxylic acid herbicides and als inhibitors |
EP3193607A4 (en) | 2014-09-15 | 2018-05-02 | Dow AgroSciences LLC | Synergistic weed control from applications of pyridine carboxylic acid herbicides and photosystem ii inhibitors |
TWI685302B (en) | 2014-09-15 | 2020-02-21 | 美商陶氏農業科學公司 | Safened herbicidal compositions comprising pyridine carboxylic acids |
AR101858A1 (en) | 2014-09-15 | 2017-01-18 | Dow Agrosciences Llc | PROTECTED HERBICIDE COMPOSITIONS THAT INCLUDE A PYRIDINCARBOXYL ACID HERBICIDE |
TWI689251B (en) | 2014-09-15 | 2020-04-01 | 美商陶氏農業科學公司 | Synergistic weed control from applications of pyridine carboxylic acid herbicides and synthetic auxin herbicides and/or auxin transport inhibitors |
GB201419828D0 (en) * | 2014-11-07 | 2014-12-24 | Syngenta Participations Ag | Herbicidal compounds |
PL238671B1 (en) | 2019-02-01 | 2021-09-20 | Przed Uslugowo Handlowe Chemirol Spolka Z Ograniczona Odpowiedzialnoscia | Herbicidal composition and method of killing weed |
CN112205418A (en) * | 2020-11-27 | 2021-01-12 | 镇江先锋植保科技有限公司 | Compound herbicide containing thifensulfuron methyl |
AR127538A1 (en) * | 2021-11-03 | 2024-02-07 | Upl Corporation Ltd | A STABLE HERBICIDE COMPOSITION |
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WO2012097629A1 (en) | 2012-07-26 |
TW201230957A (en) | 2012-08-01 |
BR112013018077A2 (en) | 2016-07-12 |
CA2834948A1 (en) | 2012-07-26 |
EP2665359A4 (en) | 2014-06-25 |
MA34427B1 (en) | 2013-08-01 |
US20120184435A1 (en) | 2012-07-19 |
CN102599152B (en) | 2016-07-06 |
CZ308313B6 (en) | 2020-05-06 |
BR112013018077B1 (en) | 2018-04-10 |
CA2834948C (en) | 2017-10-10 |
TWI527517B (en) | 2016-04-01 |
EP2665359A1 (en) | 2013-11-27 |
UA104032C2 (en) | 2013-12-25 |
FR2970399A1 (en) | 2012-07-20 |
FR2970399B1 (en) | 2013-11-29 |
CN102599152A (en) | 2012-07-25 |
BR112013018077A8 (en) | 2017-07-11 |
EP2665359B1 (en) | 2019-07-17 |
AR085078A1 (en) | 2013-09-11 |
CZ2011898A3 (en) | 2012-10-03 |
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